1. Field of the Invention
The present invention relates to new trifluoromethanesulfonanilide oxime ether derivatives useful as parasiticides, compositions containing the compounds, and methods of treatment using the compounds, especially to control animal parasites, e.g., ecto- and endoparasites such as fleas, acaridae, helminths, and nematodes. The invention also relates to the use of a combination of a parasiticide of this invention and one or more additional parasiticides or other agents useful in killing parasites.
2. Background
The control of animal parasites is essential, especially in the areas of production and companion animals. Existing methods of treatment are being compromised due to growing resistance to current commercial parasiticides, such as the benzimidazoles and ivermectins. The discovery of more effective ways to control animal parasites is therefore imperative.
Trifluoromethanesulfonanilide oxime ether derivatives have been reported in the patent literature.
In JP 08291146 trifluoromethanesulfonanilide oxime ether derivatives of Formula A have been disclosed:
wherein:
R1 is either hydrogen, C2-C10 alkanoyl or benzoyl optionally substituted by 1 or 2 substituents selected from halo or C1-C4 alkyl;
R2 is either methoxycarbonyl, acetyl, —C(═NOCH3)CH3 or C(═NOCH2CH3)CH3; and
Q is either 2-pyrimidinyl, 5-halo-2-pyrimidinyl or 6-halo-3-pyridazinyl.
These compounds have been said to show potent herbicidal activity without damaging rice seedlings.
In JP 10007657 trifluoromethanesulfonanilide oxime ether derivatives of Formula B have been disclosed:
wherein:
R1 is either hydrogen, C2-C6 alkanoyl or benzoyl;
R2 and R3 are independently selected from hydrogen, halo, nitro, cyano, (substituted)lower alkyl, (substituted)lower alkoxy, lower alkoxycarbonyl, acetyl, —C(═NOCH3)CH3 or R2 and R3 is Ph to form a naphthalene ring; and Q is either (substituted)pyrazinyl, (substituted)4-pyrimidinyl, (substituted)oxazolyl, (substituted thiazolyl, (substituted)quinoxalyl, (substituted)quinazolyl, (substituted)thiadiazolyl, (substituted)tetrazolyl, (substituted)benzoxazolyl, (substituted)benzothiazolyl, (substituted)triazolyl, (substituted)triazinyl, (substituted)pyrazolyl or (substituted)isoxazolyl.
These compounds have been said to show herbicidal activity without damaging rice plants.
In JP 10017419 and JP 10025213 trifluoromethanesulfonanilide oxime ether derivatives of Formula C have been disclosed:
wherein:
R1 is either hydrogen or C2-C5 alkanoyl; and
R2 is either hydrogen, chlorine, methoxycarbonyl or C(═NOCH3)CH3;
These compounds have been said to show herbicidal activity without damaging rice seedlings.
In JP 11060562 trifluoromethanesulfonanilide oxime ether derivatives of Formula D have been disclosed:
wherein:
R1 is (optionally)substituted alkyl or (optionally)substituted alkenyl;
R2 is either hydrogen, halo, (optionally)substituted alkoxy or (optionally)substituted alkyl;
R3 is either, hydrogen, (optionally)substituted alkyl, benzyl, acyl, alkoxycarbonyl, (optionally)substituted carbamoyl, (optionally)substituted thiocarbamoyl or —SO2R1;
Q is either —CH(NR4R5) or C(═NR6) [R4, R5 and R6 is either hydrogen, (optionally)substituted alkyl, alkenyl, alkynyl, cycloalkyl, (optionally)substituted phenyl, acyl, alkoxycarbonyl, (optionally)substituted carbamoyl, (optionally)substituted thiocarbamoyl, —SO2R1, NR7R8, or —OR9. R4 and R5, connected through a nitrogen atom, may form a nitrogen-containing heterocyclic group which possesses one or more heteroatoms]; and m is 1 to 4;
These compounds have been said to show herbicidal activity. In PCT Int. Appl. WO 2004 11, 429 trifluoromethanesulfonanilide oxime ether derivatives of Formula E have been disclosed:
wherein:
R1 is halo(C1-C6)alkyl;
R2 is either hydrogen C1-C6 alkyl or the like,
A is C1-C6 alkylene or the like;
G is O, S, NR3, NOR4 or NNR5R6;
m is 0 or 1;
X is substituted phenyl, phenoxy, or the like; and
Q is an optionally substituted heterocycle having at least one ring-constituent nitrogen atom at which the heterocycle is bonded to A.
These compounds have been said to show herbicidal activity. In the general area of insecticidal and acaricidal control, Japanese Laid-open Patent 57-156407A discloses trifluoromethanesulfonanilide compounds of Formula F:
wherein:
R is selected from alkyl, alkoxyalkyl, haloalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl or halo; and
n is 1 to 5.
A pesticidal composition which comprises the ester 2-methoxycarbonyl-4-chlorotrifluoromethanesulfonanilide (Formula G) as an active ingredient is disclosed in U.S. Pat. Nos. 6,177,465 and 6,333,022. Examples of the pests controlled by the composition include insects and acarina such as indoor mites, fleas, cockroaches and so on. The composition is said to be very effective for controlling house dust mites.

In spite of the forgoing, work in this area has continued to provide improved methods of controlling insects and acarina as well as compounds useful for the same and related purposes.
The citation of any reference herein should not be construed as an admission that such reference is available as “prior art” to the instant application.